Fluorous-tag assisted solution phase synthesis of mannose oligosaccharides

ORGN 185

Firoz A. Jaipuri, firoz@iastate.edu and Nicola L. Pohl, npohl@iastate.edu. Department of Chemistry and the Plant Sciences Institute, Iowa State University, Ames, IA 50011
A new fluorous tag-assisted solution phase strategy allows the rapid, and potentially automated, modular synthesis of carbohydrates and their direct use in forming microarrays. Application of this new concept to the synthesis of mannose oligosaccharides will be presented. Conditions for glycosylation reactions, deprotection steps, and purification using fluorous solid-phase extraction (SPE) have been developed that are amenable to automation. The fluorous tag can be used to directly form carbohydrate miocroarrays or, alternatively, a microwave-assisted deallylation results in the unmodified oligosaccharide products.